I regret selling my startup
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I regret selling my startup
1–10 of 158 posts
Re: I regret selling my startup
#2Sometimes I feel like people who sell their startup for a modest sum (hundreds of thousands to low millions) get put in a box of 'not ambitious enough' and this makes it hard to get new opportunities later as investors are seemingly all looking for unicorn founders who want to become billionaires and then achieve world domination...
I feel like any signal that you are a rational human being with well-defined, limited needs is going to be a huge turn off for investors. I don't think it's rational at all but I guess that's what decades of low interest rates does to them.
Re: I regret selling my startup
#3When I see or hear advice, I try to understand what the person's context was. Here, I feel like I don't know enough about the founder's situation to know whether any of this would be relevant to me. For example, does he have a family? How old is he? Roughly how much money did he sell for? How much profit was the business generating beforehand, and what was its trajectory?
Without knowing things like this, I can't really tell if his advice would be relevant at all for me.
Re: I regret selling my startup
#4This seems a little 'grass is greener' to me. Not sure if this is glib, but:
You can build the business again from scratch (ok, maybe you have a non compete for a while...) But you can't magic the $ you just got, out of thin air.
So he's been paid for the hard work he has done, and now if he so chooses he can do the same again, or different.
So seems like Boris is standing on the greener grass right now, to me at least. I think the post-sale reflection is naturally something that will make people question their decisions... It may be possible for Boris to Stoically rearrange his view here. There's definitely a bright shiny alternative to regret/second-guessing.
Re: I regret selling my startup
#5I never understood selling of the company unless you've been working in it for 20 years. Like isn't the idea to be your own boss?
And why sell it, if you don't have the next idea for the next business up and running? I don't know any tech startup entrepreneurs, but I do have relatives who started their own businesses but always had backup plans and diversity.
Re: I regret selling my startup
#6All good points here. For those reading just the title, the article asks to critically examine what values you hold and whether selling is compatible with those values. For me, I see selling as just another step to growing the hoard, as you state in the article, but I don't think it becomes draconic in practice.
The key in my opinion and experience is making and selling micro projects, not banking on any one taking off. That way, you can have cash flow and a hoard. Throw the hoard into VTI and let it grow while living off the cash flow (and/or reinvesting it into the business), until the investments become enough to live off of entirely, ie the 4% rule. Pieter Levels or Daniel Vassallo are good examples of this.
Just keep trying, don't be saddened by another startup failure, at least you already have one sold which is a lot more than most founders can say.
I'm also in NYC, let me know if you want to chat, as you stated at the end of the post.
Re: I regret selling my startup
#7I never understood selling of the company unless you've been working in it for 20 years. Like isn't the idea to be your own boss? And why sell it, if you don't have the next idea for the next business up and running? I don't know any tech startup entrepreneurs, but I do have relatives who started their own businesses but always had backup plans and diversity.
The article covers this, one can just get tired of it all and want to divest. It's also better to be diverse in your investments rather than putting all your eggs in one basket and hoping it doesn't fail after 20 years, which can definitely happen. Sell, live off the money you made from selling, and take a break until you get your next few ideas.
Re: I regret selling my startup
#8All good points here. For those reading just the title, the article asks to critically examine what values you hold and whether selling is compatible with those values. For me, I see selling as just another step to growing the hoard, as you state in the article, but I don't think it becomes draconic in practice. The key in my opinion and experience is making and selling micro projects, not banking on any one taking o…
Perhaps I am unfamiliar with this usage of the word horde, but is it possible that you mean hoard?
Re: I regret selling my startup
#9Sometimes I feel like people who sell their startup for a modest sum (hundreds of thousands to low millions) get put in a box of 'not ambitious enough' and this makes it hard to get new opportunities later as investors are seemingly all looking for unicorn founders who want to become billionaires and then achieve world domination... I feel like any signal that you are a rational human being with well-defined, limited…
Why do they have to take VC? The founder in this article bootstrapped their business and sold, they can always do that again.
Re: I regret selling my startup
#10I never understood selling of the company unless you've been working in it for 20 years. Like isn't the idea to be your own boss? And why sell it, if you don't have the next idea for the next business up and running? I don't know any tech startup entrepreneurs, but I do have relatives who started their own businesses but always had backup plans and diversity.
It all depends on the multiple. If someone is giving you 3 years of profit up-front, that's probably not worth it. If they're giving you 10 years of profit, that could make sense. You avoid having to work for that period of time, and you avoid the risk that something could go wrong (with the company, the economy, the sector) during that time. It also allows you to diversify your assets.